Ethyl Acetate → HCID 70981944, compound

HRID 572433Notes

Reaction equation

HRID 572433 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH2:12][CH2:11][CH2:10][CH:9]=1.C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC.[Pt]=O>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 2

HCID 8857Ethyl AcetateHCID 709821203-Bromo-4-cyclopent-1-enyl-pyridine

Product 1

HCID 70981944HCID 70981944, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

Platinum oxide (20 mg) was added to a mixture of 3-bromo-4-cyclopent-1-enyl-pyridine (I-34b: 140 mg, 0.622 mmol) in toluene (5 mL) and stirred overnight under hydrogen atmosphere. The reaction was monitored by TLC (20% ethyl acetate in hexane). The reaction mixture was filtered through celite pad and washed with toluene and concentrated to afford crude product. Purification by column chromatography (8% ethyl acetate in hexane) afforded 98 mg of the product (71% yield).

Workup

  1. filtrationThe reaction mixture was filtered through celite pad
  2. washwashed with toluene
  3. concentrationconcentrated
  4. customto afford crude product
  5. customPurification by column chromatography (8% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-9442f04f3ef04f95abebe939af6d377e
Source dataset
uspto-grants-2015_05
Patent number
US09029399B2

Reaction notes

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